Pesticide Thiazolyloxy Substituted Phenylamidine Derivatives

ABSTRACT

The present invention relates to aryloxy substituted phenylamidine derivatives of formula (I) wherein the substituents are as in the description, their process of preparation, their use as fungicide or insecticide active agents, particularly in the form of fungicide or insecticide compositions, and methods for the control of phytopathogenic fungi or damaging insects, notably of plants, using these compounds or compositions (I).

The present invention relates to aryloxy substituted phenylamidine derivatives, their process of preparation, their use as fungicide or insecticide active agents, particularly in the form of fungicide or insecticide compositions, and methods for the control of phytopathogenic fungi or damaging insects, notably of plants, using these compounds or compositions.

In international patent application WO-00/46184 certain phenyl-amidine derivatives are disclosed. However, this document does not specifically disclose nor suggest to select such compounds wherein the phenyl ring is substituted according to the invention thus allowing an unexpected and significantly higher fungicide activity.

It is always of high-interest in agriculture to use novel pesticide compounds in order to avoid or to control the development of resistant strains to the active ingredients. It is also of high-interest to use novel compounds being more active than those already known, with the aim of decreasing the amounts of active compound to be used, whilst at the same time maintaining an effectiveness at least equivalent to the already known compounds.

In the same way, it is also always of high-interest to use novel insecticide, nematocide or acaricide agents to control damaging insects or other damaging organisms.

We have now found a new family of compounds which possess the above mentioned effects or advantages.

Accordingly, the present invention provides amidine derivatives of formula (I):

wherein

-   -   R¹ represents H, a substituted or non substituted C₁-C₁₂-alkyl,         a substituted or non substituted C₂-C₁₂-alkenyl, a substituted         or non substituted C₂-C₁₂-alkynyl, SH or a substituted or non         substituted S—C₁-C₁-C₁₂-alkyl;     -   R² represents a substituted or non substituted C₁-C₁₂-alkyl;     -   R³ represents a substituted or non substituted C₂-C₁₂-alkyl,         substituted or non substituted C₃-C₆-cycloalkyl, substituted or         non substituted C₂-C₁₂-alkenyl, substituted or non substituted         C₂-C₁₂-alkynyl, halogeno-C₁-C₁₂-alkyl; or     -   R¹ and R², R¹ and R³ or R² and R³ can form together a         substituted or non substituted 5- to 7-membered heterocycle;     -   R⁴ represents a substituted or non substituted C₁-C₁₂-alkyl, a         halogen atom, halogeno-C₁-C₁₂-alkyl, substituted or non         substituted O—C₁-C₁₂-alkyl or cyano;     -   R⁵ represents H, a substituted or non substituted C₁-C₁₂-alkyl,         a halogen atom, halogeno-C₁-C₁₂-alkyl, substituted or non         substituted O—C₁-C₁₂-alkyl or cyano;     -   R⁶ represents a heterocycle selected in the list consisting of

-   -   R⁷ represents H, halogen, nitro, cyano; substituted or non         substituted phenyl, substituted or non substituted benzyl;         C₁-C₈-alkyl, C₁-C₈-alkoxy, C₁-C₈-alkylthio, C₁-C₆-halogenalkyl,         C₁-C₆-halogenalkoxy or C₁-C₆-halogenalkylthio;         C₁-C₈—S(O)_(m)R¹¹; C₁-C₈-alkyl-SO₂NR¹²R¹³; C₁-C₈-alkyl-COR¹⁴;         —CR¹⁵═N—O—R¹⁶, S(O)_(m)R¹¹, SO₂NR¹²R¹³, COR¹⁴;     -   R⁸ represents H, halogen, cyano; substituted or non substituted         phenyl, substituted or non substituted benzyl; C₁-C₈-alkyl,         C₁-C₈-alkoxy, C₁-C₈-alkylthio, C₁-C₆-halogenalkyl,         C₁-C₆-halogenalkoxy or C₁-C₆-halogenalkylthio;         C₁-C₈-alkyl-COR¹⁴; —CR¹⁵═N—O—R¹⁶, COR¹⁴;     -   R⁷ and R⁸ can form a carbocycle, which can be saturated,         unsaturated or aromatic and substituted or non substituted by         halogen, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, or C₁-C₄-alkoxyalkyl     -   R⁹ represents H, halogen, cyano; substituted or non substituted         phenyl, substituted or non substituted benzyl; C₁-C₈-alkyl,         C₁-C₈-alkoxy, C₁-C₈-alkylthio, C₁-C₆-halogenalkyl,         C₁-C₆-halogenalkoxy or C₁-C₆-halogenalkylthio;         C₁-C₈-alkyl-COR¹⁴; —CR¹⁵═N—O—R¹⁶, COR¹⁴;     -   R¹⁰ represents H, halogen, cyano; substituted or non substituted         phenyl, substituted or non substituted benzyl, substituted or         non substituted pyridyl; C₁-C₈-alkyl, C₁-C₈-alkoxy,         C₁-C₈-alkylthio, C₁-C₆-halogenalkyl, C₁-C₆-halogenalkoxy or         C₁-C₆-halogen-alkylthio; C₁-C₈-alkyl-S(O)_(m)R¹¹;         C₁-C₈-alkyl-SO₂NR¹²R¹³; C₁-C₈-alkyl-COR¹⁴; —CR¹⁵═N—O—R¹⁶,         S(O)_(m)R¹¹, SO₂NR¹²R¹³, COR¹⁴:     -   m represents 0, 1 or 2;     -   R¹¹ represents C₁-C₈-alkyl, C₃-C₆-cycloalkyl;     -   R¹² represents H, C₁-C₈-alkyl, C₃-C₆-cycloalkyl     -   R¹³ represents H, C₁-C₈-alkyl, C₃-C₆-cycloalkyl;     -   R¹⁴ represents H, substituted or non substituted, branched or         linear C₁-C₈-alkyl, C₁-C₈-alkoxy;     -   R¹⁵ represents H, C₁-C₈-alkyl, C₃-C₆-cycloalkyl;     -   R¹⁶ represents H, C₁-C₈-alkyl, C₃-C₆-cycloalkyl, C₁-C₈-alkoxy,         substituted or non substituted benzyl;     -   R¹² and R¹³ can form a 5- or 6-membered heterocycle, which can         further comprise one or more heteroatoms selected in the list         consisting of O, N, S;     -   R¹⁵ and R¹⁶ can form a heterocyclic 5- or 6-membered ring,         including further heteroatoms, like O, S, N;         as well as salts, N-oxides, metallic complexes, metalloidic         complexes and optically active or geometric isomers thereof.

Any of the compounds according to the invention can exist in one or more optical, geometric or chiral isomer forms depending on the number of asymmetric centres in the compound. The invention thus relates equally to all the optical isomers and to their racemic or scalemic mixtures (the term “scalemic” denotes a mixture of enantiomers in different proportions), and to the mixtures of all the possible stereoisomers, in all proportions. The diastereoisomers and/or the optical isomers can be separated according to the methods which are known per se by the man ordinary skilled in the art.

Any of the compounds according to the invention can also exist in one or more geometric isomer forms depending on the number of double bonds in the compound. The invention thus relates equally to all geometric isomers and to all possible mixtures, in all proportions. The geometric isomers can be separated according to general methods, which are known per se by the man ordinary skilled in the art.

For the compounds according to the invention, halogen means either one of fluorine, bromine, chlorine or iodine and heteroatom can be nitrogen, oxygen or sulphur.

Preferred compounds of formula (I) according to the invention are those wherein R¹ represents H; C₁-C₁₂-alkyl, preferably C₁-C₁₂-alkyl like methyl; or SH.

Other preferred compounds of formula (I) according to the invention are those wherein R² represents methyl.

Still other preferred compounds of formula (I) according to the invention are those wherein R³ represents C₂-C₁₂-alkyl, preferably a non substituted C₂-C₄-alkyl like ethyl, n-propyl, i-propyl; C₂-C₁₂-alkenyl, preferably C₃-C₄-alkenyl like propenyl or allyl; C₃-C₆-cycloalkyl like cyclopropyl.

Still other preferred compounds of formula (I) according to the invention are those wherein R² and R³ can form together a substituted or non substituted 5- to 7-membered heterocycle, preferably a 6-membered heterocycle, more preferably a piperidinyl or a pyrrolidinyl, even more preferably a 2-alkylated-pyrrolidinyl like a 2-methyl-pyrrolidinyl.

Still other preferred compounds of formula (I) according to the invention are those wherein R⁴ represents a C₁-C₁₂-alkyl, preferably a non substituted C₁-C₁₂-alkyl like methyl and ethyl; a halogen atom like a fluorine and a chlorine atom; trifluoromethyl.

Still other preferred compounds of formula (I) according to the invention are those wherein R⁵ represents H, C₁-C₁₂-alkyl, preferably a non substituted C₁-C₁₂-alkyl like methyl and ethyl; a halogen atom like a fluorine and a chlorine atom; trifluoromethyl.

Still other preferred compounds of formula (I) according to the invention are those wherein R⁷ represents H, Cl, Br, I, nitro, cyano; phenyl; phenyl substituted by F, Cl, Br, I, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy; benzyl; benzyl substituted by F, Cl, Br, I, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy; C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-halogenalkyl, C₁-C₄-halogenalkoxy or C₁-C₄-halogenalkylthio; C₁-C₄-alkyl-S(O)_(m)R¹¹; C₁-C₄-alkyl-SO₂NR¹²R¹³; C₁-C₄-alkyl-COR¹⁴; —CR¹⁵═N—O—R¹⁶, S(O)_(m)R¹¹, SO₂NR¹²R¹³, COR¹⁴.

Still other preferred compounds of formula (I) according to the invention are those wherein R⁸ represents H, Cl, Br, I, cyano; phenyl; phenyl substituted by F, Cl, Br, I, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy; benzyl; benzyl substituted by F, Cl, Br, I, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy; C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-halogenalkyl, C₁-C₄-halogenalkoxy or C₁-C₄-halogenalkylthio; C₁-C₄-alkyl-COR¹⁴; —CR¹⁵═N—O—R¹⁶, COR¹⁴.

Still other preferred compounds of formula (I) according to the invention are those wherein R⁷ and R⁸ form a carbocycle, which can be saturated, unsaturated or aromatic and substituted or non substituted by halogen, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, or C₁-C₄-alkoxyalkyl.

Still other preferred compounds of formula (I) according to the invention are those wherein R⁹ represents H, Cl, Br, I, cyano; phenyl; phenyl substituted by F, Cl, Br, I, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy; benzyl; benzyl substituted by F, Cl, Br, I, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy; C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-halogenalkyl, C₁-C₄-halogenalkoxy or C₁-C₄-halogenalkylthio; C₁-C₄-alkyl-COR¹⁴; —CR¹⁵═N—O—R¹⁶, COR¹⁴.

Still other preferred compounds of formula (I) according to the invention are those wherein R¹⁰ represents H, Cl, Br, I, cyano; phenyl; phenyl substituted by F, Cl, Br, I, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy; benzyl; benzyl substituted by F, Cl, Br, I, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy; pyridyl; pyridyl substituted by F, Cl, Br, I, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy; C₁-C₆-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-halogenalkyl, C₁-C₄-halogen-alkoxy or C₁-C₄-halogenalkylthio; C₁-C₄-alkyl-S(O)_(m)R¹¹; C₁-C₄-alkyl-SO₂NR¹²R¹³; C₁-C₄-alkyl-COR¹⁴; —CR¹⁵═N—O—R¹⁶, S(O)_(m)R¹¹, SO₂NR¹²R¹³, COR¹⁴.

Still other preferred compounds of formula (I) according to the invention are those wherein R¹¹ represents C₁-C₈-alkyl, C₃-C₆-cycloalkyl.

Still other preferred compounds of formula (I) according to the invention are those wherein R¹² represents H, C₁-C₈-alkyl, C₃-C₆-cycloalkyl.

Still other preferred compounds of formula (I) according to the invention are those wherein R¹³ represents H, C₁-C₈-alkyl, C₃-C₆-cycloalkyl.

Still other preferred compounds of formula (I) according to the invention are those wherein R¹⁴ represents H, branched or linear C₁-C₈-alkyl, C₁-C₈-alkoxy.

Still other preferred compounds of formula (I) according to the invention are those wherein R¹⁵ represents H, C₁-C₈-alkyl, C₃-C₆-cycloalkyl.

Still other preferred compounds of formula (I) according to the invention are those wherein R¹⁶ represents H, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, benzyl; benzyl substituted by halogen, C₁-C₄-alkyl or C₁-C₄-halogenoalkyl.

Still other preferred compounds of formula (I) according to the invention are those wherein R¹² and R¹³ form a 5- or 6-membered heterocycle, which can further comprise one or more heteroatoms selected in the list consisting of O, N, S.

Still other preferred compounds of formula (I) according to the invention are those wherein R¹⁵ and R¹⁶ can form a 5- or 6-membered heterocycle comprising further heteroatoms, like O, S, N.

The above mentioned preferences with regard to the substituents of the compounds according to the invention can be combined in various manners. These combinations of preferred features thus provide sub-classes of compounds according to the invention. Examples of such sub-classes of preferred compounds according to the invention can combine:

-   -   preferred features of R¹ with preferred features of R² to R⁶ or         to R¹⁶ where applicable;     -   preferred features of R² with preferred features of R¹ to R⁶ or         to R¹⁶ where applicable;     -   preferred features of R³ with preferred features of R¹ to R⁶ or         to R¹⁶ where applicable;     -   preferred features of R⁴ with preferred features of R¹ to R⁶ or         to R¹⁶ where applicable;     -   preferred features of R⁵ with preferred features of R¹ to R⁶ or         to R¹⁶ where applicable.

In these combinations of preferred features of the substituents of the compounds according to the invention, the said preferred features can also be selected among the more preferred features of each of m, n and R¹ to R¹¹ so as to form most preferred subclasses of compounds according to the invention.

The present invention also relates to a process for the preparation of a compound of formula (I). Generally, the preparation of compound of formula (I) according to the invention can be carried out as illustrated by scheme 1 and scheme 1a.

In schemes 1 and 1a, formula (IV)

wherein

-   -   Y represents C—R⁸ (see formula (IVa)), C—R¹⁰ (see formula         (IVc)), or N (see formula (IVb)),     -   Z represents C—R⁷ (see formula (IVa)), C—R⁹ (see formula (IVb)),         or N (see formula (IVc)).     -   R⁷, R⁸, R⁹ and R¹⁰ are as herein-defined,     -   X represents halogen, triflate, SOMe, mesylate or tosylate.

Thus according to a further aspect according to the invention, there is provided a process (a) for the preparation of aniline derivatives of formulae (I) and (II) by reacting aminophenol derivatives of formula (III) or amidine derivatives of formula (IX)

wherein

-   -   R¹, R², R³, R⁴ and R⁵ are as herein-defined,         with thiazole derivatives or thiadiazole derivatives         (1,3,4-thiadiazoles or 1,3,5-thiadiazoles) of formula (IV) or         (IVa), (IVb) and (IVc), respectively,

wherein

-   -   Z, Y R⁷, R⁸, R⁹ and R¹⁰ are as herein-defined     -   X represents halogen, triflate, SOMe, mesylate or tosylate.

Process (a) according to the invention can further comprise one or more of the following characteristics:

-   -   presence of a base;     -   presence of an inert organic diluent;     -   presence of a catalyst.

Process (a) according to the invention is carried out using 4-amino-2,5-dimethylphenol, 2,4,5-trichloro-1,3-thiazole and a base as starting materials. Process (a) can be conducted according to scheme 2.

Formula (IV) or formulae (IVa), (IVb) and (IVc), respectively, provide general definitions for the thiazole derivatives and thiadizole derivatives useful as starting materials for carrying out process (a) according to the invention.

Formulae (III) and (IX) provide a general definition of the aminophenol derivatives or amidine derivatives useful as starting materials for carrying out process (a) according to the invention. In this formula, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, X, Y and Z preferably represent substituents as herein-defined in connection with the description of compounds of formula (I) according to the invention.

Amidine derivatives of formula (I) and (IX) can be prepared by a further process according to the invention. Various alternatives of process (b) according to the invention can be considered, they are defined as process (b1), process (b2) and process (b3) according to the invention. Process (b) according to the invention comprises reacting aniline derivatives of formulae (II) and (III) with different reagents thus defining processes (b1), (b2) and (3) respectively

wherein

-   -   R⁴, R⁶, Y and Z are as herein-defined.

Process (b1) is carried out further using amide derivatives of formula (VI)

wherein

-   -   R¹, R², R³ are as herein-defined.

Process (b1) according to the invention can further comprise one or more of the following characteristics:

-   -   presence of a halogenation agent, like PCl₅, PCl₃, POCl₃, SOCl₂;     -   presence of a diluent.

Process (b1) according to the invention is carried out using 4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylaniline, piperidin-2-one and phosphoric trichloride as starting materials. Process (b1) can be conducted according to scheme 3.

Formula (II) provides a general definition of the biphenylamine derivatives useful as starting materials for carrying out process (b1) according to the invention. In this formula R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, Y and Z preferably represent substituents as herein-defined in connection with the description of compounds of formula (I) according to the invention.

Process (b2) is carried out further using amino-acetal derivatives of formula (V)

wherein

-   -   R¹, R², R³ are as herein-defined;     -   B¹ and B² represent each alkyl or together cycloalkyl.

Process (b2) according to the invention can further comprise one or more of the following characteristics:

-   -   presence of an acid or base;     -   presence of a diluent.

Process (b2) according to the invention is carried out using 4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylaniline and N-(dimethoxymethyl)-N-methylethanamine as starting materials. Process (b2) can be conducted according to scheme 4.

Process (b3) is carried out further using amine derivatives of formula (VII)

wherein

-   -   R² and R³ are as herein-defined;         in presence of orthoester derivatives of formula (VIII)

wherein

-   -   R¹ is as herein-defined;     -   B¹, B² and B³ represent each alkyl.

Formulae (II) and (III) provide general definitions of the amine derivatives useful as starting materials for carrying out process (b3) according to the invention. In this formulae, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, Y and Z preferably represent substituents as herein-defined in connection with the description of compounds of formula (I) according to the invention.

Process (b3) according to the invention is carried out using 4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylaniline, trimethyl-ortho-ester and N-methyl-ethanamine as starting materials and an acid.

Process (d3) can be conducted according to scheme 5.

Formulae (II) and (III) provide general definitions of the amine derivatives useful as starting materials for carrying out process (b3) according to the invention. In these formulae, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, Y and Z preferably represent substituents as herein-defined in connection with the description of compounds of formula (I) according to the invention.

Processes (b), (b1), (b2) or (b3) according to the invention can further comprise one or more of the following characteristics:

-   -   presence of a acid or base;     -   presence of a diluent.

Amidine derivatives of formula (I) can be prepared by a further process (c) according to the invention by reacting amidine derivatives of formula (I)

wherein

-   -   Y or Z represent C—COR₁₄ and R¹, R², R³, R⁴ and R⁵ are as         herein-defined with hydroxylamines or salts thereof,         respectively

wherein R¹⁶ is as herein-defined.

Process (c) according to the invention can further comprise one or more of the following characteristics:

-   -   presence of an acid or a base;     -   presence of an inert organic diluent;     -   presence of a catalyst.

Process (c) according to the invention is carried out using N′-{4-[(5-acetyl-4-methyl-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide and 3-(aminooxy)prop-1-ene hydrochloride as starting materials.

Process (c) can be conducted according to scheme 6.

Suitable diluents for carrying out process (a) according to the invention are all customary inert organic solvents. Preference is given to using aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers, such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; nitriles, such as acetonitrile, propionitrile, n- or iso-butyronitrile or benzonitrile; amides, such as N,N-dimethyl-formamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethyl-phosphoric triamide; mixtures thereof with water or pure water.

Suitable diluents for carrying out processes (b1), (b2), (b3) and (c) according to the invention are in each case all customary inert organic solvents. Preference is given to using aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; ethers, such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; nitriles, such as acetonitrile, propionitrile, n- or iso-butyronitrile or benzonitrile; amides, such as N,N-dimethylformamide, N,N-dimethyl-acetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; esters, such as methyl acetate or ethyl acetate; sulphoxides, such as dimethylsulphoxide; or sulphones, such as sulpholane; alcohols, such as methanol, ethanol, n- or iso-propanol, n-, iso-, sec- or tert-butanol, ethanediol, propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene-glycolmonomethylether, diethyleneglycolmonoethylether; mixtures thereof with water or pure water.

Suitable acid binders for carrying out process (a) according to the invention are all inorganic and organic bases customary for such reactions. Preference is given to using alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as sodium hydride, sodium amide, lithiium diisoproylamide, sodium methanolate, sodium ethanolate, potassium tert-butanolate, sodium acetate, potassium acetate, calcium acetate, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate, or ammonium carbonate; and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dimethyl-benzylamine pyridine, N-methylpiperidine, N-methylmorpholine, N,N-dimethylamino-pyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or di-azabicycloundecene (DBU).

Suitable acids for carrying out process (b3) according to the invention are all inorganic and organic acids customary for such reactions. Preference is given to using para-toluene sulfonic acid, methane sulfonic acid, hydrochloric acid (gas, aqueous or organic solution) or sulphuric acid.

Suitable condensing agents for carrying out process (b1) according to the invention are all condensing agents customary for such amidation reactions. Preference is given to using acid halide former, such as phosgene, phosphorous tribromide, phosphorous trichloride, phosphorous pentachloride, phosphorous trichloride oxide or thionyl chloride; anhydride former, such as ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate or methanesulfonyl chloride; carbodiimides, such as N,N′-dicyclohexylcarbodiimide (DCC) or other customary condensing agents, such as phosphorous pentoxide, polyphosphoric acid, N,N′-carbonyldiimidazole, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), triphenylphosphine/tetrachloromethane or bromo-tripyrrolidino-phosphonium-hexafluorophosphate.

When carrying out processes (a), (b) and (c) according to the invention, the reaction temperature can be varied within a relatively wide range. In general, the process is carried out at temperatures between from 0° C. to 150° C., preferably from 0° C. to 120° C., particularly preferably from 10° C. to 90° C.

Compounds of formula (I) according to the invention can be prepared according to the herein described processes. It will nevertheless be understood that, on the basis of his general knowledge and of available publications, the skilled worker will be able to adapt these processes according to the specifics of each of the compounds which it is desired to synthesise.

In a further aspect, the present invention also relates to a fungicide or insecticide composition comprising an effective and non-phytotoxic amount of an active compound of formula (I). The expression “effective and non-phytotoxic amount” means an amount of composition according to the invention which is sufficient to control or destroy the fungi present or liable to appear on the crops, and which does not entail any appreciable symptom of phytotoxicity for the said crops. Such an amount can vary within a wide range depending on the fungus to be controlled, the type of crop, the climatic conditions and the compounds included in the fungicide composition according to the invention.

This amount can be determined by systematic field trials, which are within the capabilities of a person skilled in the art.

Thus, according to the invention, there is provided a fungicide composition comprising, as an active ingredient, an effective amount of a compound of formula (I) as herein-defined and an agriculturally acceptable support, carrier or filler.

According to the invention, the term “support” denotes a natural or synthetic, organic or inorganic compound with which the active compound of formula (I) is combined or associated to make it easier to apply, notably to the parts of the plant. This support is thus generally inert and should be agriculturally acceptable. The support may be a solid or a liquid. Examples of suitable supports include clays, natural or synthetic silicates, silica, resins, waxes, solid fertilisers, water, alcohols, in particular butanol, organic solvents, mineral and plant oils and derivatives thereof. Mixtures of such supports may also be used.

The composition according to the invention may also comprise additional components. In particular, the composition may further comprise a surfactant. The surfactant can be an emulsifier, a dispersing agent or a wetting agent of ionic or non-ionic type or a mixture of such surfactants. Mention may be made, for example, of polyacrylic acid salts, lignosulphonic acid salts, phenolsulphonic or naphthalenesulphonic acid salts, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (in particular alkylphenols or arylphenols), salts of sulphosuccinic acid esters, taurine derivatives (in particular alkyl taurates), phosphoric esters of polyoxyethylated alcohols or phenols, fatty acid esters of polyols, and derivatives of the present compounds containing sulphate, sulphonate and phosphate functions. The presence of at least one surfactant is generally essential when the active compound and/or the inert support are water-insoluble and when the vector agent for the application is water. Preferably, surfactant content may be comprised from 5% to 40% by weight of the composition.

Optionally, additional components may also be included, e.g. protective colloids, adhesives, thickeners, thixotropic agents, penetration agents, stabilisers, sequestering agents. More generally, the active compounds can be combined with any solid or liquid additive, which complies with the usual formulation techniques.

In general, the composition according to the invention may contain from 0.05 to 99% by weight of active compound, preferably 10 to 70% by weight.

Compositions according to the invention can be used in various forms such as aerosol dispenser, bait (ready for use), bait concentrate, block bait, capsule suspension, cold fogging concentrate, dustable powder, emulsifiable concentrate, emulsion oil in water, emulsion water in oil, encapsulated granule, fine granule, flowable concentrate for seed treatment, gas (under pressure), gas generating product, grain bait, granular bait, granule, hot fogging concentrate, macrogranule, microgranule, oil dispersible powder, oil miscible flowable concentrate, oil miscible liquid, paste, plant rodlet, plate bait, powder for dry seed treatment, scrap bait, seed coated with a pesticide, smoke candle, smoke cartridge, smoke generator, smoke pellet, smoke rodlet, smoke tablet, smoke tin, soluble concentrate, soluble powder, solution for seed treatment, suspension concentrate (=flowable concentrate), tracking powder, ultra low volume (ulv) liquid, ultra low volume (ulv) suspension, vapour releasing product, water dispersible granules or tablets, water dispersible powder for slurry treatment, water soluble granules or tablets, water soluble powder for seed treatment and wettable powder.

These compositions include not only compositions which are ready to be applied to the plant or seed to be treated by means of a suitable device, such as a spraying or dusting device, but also concentrated commercial compositions which must be diluted before application to the crop.

The compounds according to the invention can also be mixed with one or more insecticide, fungicide, bactericide, attractant, acaricide or pheromone active substance or other compounds with biological activity. The mixtures thus obtained have a broadened spectrum of activity.

The mixtures with other fungicide compounds are particularly advantageous. Examples of suitable fungicide mixing partners may be selected in the following lists:

-   -   B1) a compound capable to inhibit the nucleic acid synthesis         like benalaxyl, benalaxyl-M, bupirimate, chiralaxyl, clozylacon,         dimethirimol, ethirimol, furalaxyl, hymexazol, metalaxyl,         metalaxyl-M, ofurace, oxadixyl, oxolinic acid;     -   B2) a compound capable to inhibit the mitosis and cell division         like benomyl, carbendazim, diethofencarb, fuberidazole,         pencycuron, thiabendazole thiophanate-methyl, zoxamide;     -   B3) a compound capable to inhibit the respiration for example     -   as CI-respiration inhibitor like diflumetorim;     -   as CII-respiration inhibitor like boscalid, carboxin, fenfuram,         flutolanil, furametpyr, mepronil, oxycarboxine, penthiopyrad,         thifluzamide;     -   as CIII-respiration inhibitor like azoxystrobin, cyazofamid,         dimoxystrobin, enestrobin, famoxadone, fenamidone,         fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin,         pyraclostrobin, picoxystrobin, trifloxystrobin;     -   B4) a compound capable of to act as an uncoupler like dinocap,         fluazinam;     -   B5) a compound capable to inhibit ATP production like fentin         acetate, fentin chloride, fentin hydroxide, silthiofam;     -   B6) a compound capable to inhibit AA and protein biosynthesis         like andoprim, blasticidin-S, cyprodinil, kasugamycin,         kasugamycin hydrochloride hydrate, mepanipyrim, pyrimethanil;     -   B7) a compound capable to inhibit the signal transduction like         fenpiclonil, fludioxonil, quinoxyfen;     -   B8) a compound capable to inhibit lipid and membrane synthesis         like chlozolinate, iprodione, procymidone, vinclozolin,         pyrazophos, edifenphos, iprobenfos (IBP), isoprothiolane,         tolclofos-methyl, biphenyl, iodocarb, propamocarb,         propamocarb-hydrochloride;     -   B9) a compound capable to inhibit ergosterol biosynthesis like         fenhexamid, azaconazole, bitertanol, bromuconazole,         cyproconazole, diclobutrazole, difenoconazole, diniconazole,         diniconazole-M, epoxiconazole, etaconazole, fenbuconazole,         fluquinconazole, flusilazole, flutriafol, furconazole,         furconazole-cis, hexaconazole, imibenconazole, ipconazole,         metconazole, myclobutanil, paclobutrazol, penconazole,         propiconazole, prothioconazole, simeconazole, tebuconazole,         tetraconazole, triadimefon, triadimenol, triticonazole,         uniconazole, voriconazole, imazalil, imazalil sulfate,         oxpoconazole, fenarimol, flurprimidol, nuarimol, pyrifenox,         triforine, pefurazoate, prochloraz, triflumizole, viniconazole,         aldimorph, dodemorph, dodemorph acetate, fenpropimorph,         tridemorph, fenpropidin, spiroxamine, naftifine, pyributicarb,         terbinafine;     -   B10) a compound capable to inhibit cell wall synthesis like         benthiavalicarb, bialaphos, dimethomorph, flumorph,         iprovalicarb, polyoxins, polyoxorim, validamycin A;     -   B11) a compound capable to inhibit melanine biosynthesis like         carpropamid, diclocymet, fenoxanil, phtalide, pyroquilon,         tricyclazole;     -   B12) a compound capable to induce a host defence like         acibenzolar-S-methyl, probenazole, tiadinil;     -   B13) a compound capable to have a multisite action like         captafol, captan, chlorothalonil, copper preparations such as         copper hydroxide, copper naphthenate, copper oxychloride, copper         sulphate, copper oxide, oxine-copper and Bordeaux mixture,         dichlofluanid, dithianon, dodine, dodine free base, ferbam,         fluorofolpet, folpet, guazatine, guazatine acetate,         iminoctadine, iminoctadine albesilate, iminoctadine triacetate,         mancopper, mancozeb, maneb, metiram, metiram zinc, propineb,         sulphur and sulphur preparations including calcium polysulphide,         thiram, tolylfluanid, zineb, ziram;     -   B14) a compound selected in the following list: amibromdole,         benthiazole, bethoxazin, capsimycin, carvone, chinomethionat,         chloropicrin, cufraneb, cyflufenamid, cymoxanil, dazomet,         debacarb, diclomezine, dichlorophen, dicloran, difenzoquat,         difenzoquat methylsulphate, diphenylamine, ethaboxam, ferimzone,         flumetover, flusulfamide, fosetyl-aluminium, fosetyl-calcium,         fosetyl-sodium, fluopicolide, fluoroimide, hexachlorobenzene,         8-hydroxyquinoline sulfate, irumamycin, methasulphocarb,         metrafenone, methyl isothiocyanate, mildiomycin, natamycin,         nickel dimethyldithiocarbamate, nitrothal-isopropyl,         octhilinone, oxamocarb, oxyfenthiin, pentachlorophenol and         salts, 2-phenylphenol and salts, phosphorous acid and its salts,         piperalin, propanosine-sodium, proquinazid, pyrrolnitrine,         quintozene, tecloftalam, tecnazene, triazoxide, trichlamide,         zarilamid and 2,3,5,6-tetrachloro-4-(methylsulfonyl)-pyridine,         N-(4-Chloro-2-nitrophenyl)-N-ethyl-4-methyl-benzenesulfonamide,         2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide,         2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridincarboxamide,         3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine,         cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazole-1-yl)-cycloheptanol,         methyl         1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,         3,4,5-trichloro-2,6-pyridinedicarbonitrile, Methyl         2-[[[cyclopropyl[(4-methoxyphenyl)imino]methyl]thio]methyl]-.alpha.-(methoxymethylene)-benzeneacetate,         4-Chloro-alpha-propynyloxy-N-[2-[3-methoxy-4-(2-propynyloxy)phenyl]ethyl]-benzeneacetamide,         (2S)—N-[2-[4-[[3-(4-chlorophenyl)-2-propynyl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(methylsulfonyl)amino]-butanamide,         5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidine,         5-chloro-6-(2,4,6-trifluorophenyl)-N-[(1R)-1,2,2-trimethylpropyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine,         5-chloro-N-[(1R)-1,2-dimethylpropyl]-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,         N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloronicotinamide,         N-(5-bromo-3-chloropyridin-2-yl)methyl-2,4-dichloronicotinamide,         2-butoxy-6-iodo-3-propyl-benzopyranon-4-one,         N-{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide,         N-(3-ethyl-3,5,5-trimethyl-cyclohexyl)-3-formylamino-2-hydroxy-benzamide,         2-[[[[1-[3(1Fluoro-2-phenylethyl)oxy]phenyl]ethylidene]amino]oxy]methyl]-alpha-(methoxyimino)-N-methyl-alphaE-benzeneacetamide,         N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}-2-(trifluoromethyl)benzamide,         N-(3′,4′-dichloro-5-fluorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,         2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylacetamide,         1-[(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl-1H-imidazole-1-carboxylic         acid,         O-[1-[(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl]-1H-imidazole-1-carbothioic         acid.

The composition according to the invention comprising a mixture of a compound of formula (I) with a bactericide compound may also be particularly advantageous. Examples of suitable bactericide mixing partners may be selected in the following list: bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulphate and other copper preparations.

The compound of formula (I) and the fungicide composition according to the invention can be used to curatively or preventively control the phytopathogenic fungi of plants or crops. Thus, according to a further aspect of the invention, there is provided a method for curatively or preventively controlling the phytopathogenic fungi of plants or crops characterised in that a compound of formula (I) or a fungicide composition according to the invention is applied to the seed, the plant or to the fruit of the plant or to the soil wherein the plant is growing or wherein it is desired to grow.

In the same manner, the compound of formula (I) and the insecticide composition according to the invention can be used to curatively or preventively control damaging insects, notably of plants or crops. Thus, according to a further aspect of the invention, there is provided a method for curatively or preventively controlling damaging insects, notably of plants or crops, characterised in that a compound of formula (I) or an insecticide composition according to the invention is applied to the seed, the plant or to the fruit of the plant or to the soil wherein the plant is growing or wherein it is desired to grow.

The method of treatment according to the invention may also be useful to treat propagation material such as tubers or rhizomes, but also seeds, seedlings or seedlings pricking out and plants or plants pricking out. This method of treatment can also be useful to treat roots. The method of treatment according to the invention can also be useful to treat the overground parts of the plant such as trunks, stems or stalks, leaves, flowers and fruit of the concerned plant.

Among the plants that can be protected by the method according to the invention, mention may be made of cotton; flax; vine; fruit or vegetable crops such as Rosaceae sp. (for instance pip fruit such as apples and pears, but also stone fruit such as apricots, almonds and peaches), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (for instance banana trees and plantins), Rubiaceae sp., Theaceae sp., Sterculiceae sp., Rutaceae sp. (for instance lemons, oranges and grapefruit); Solanaceae sp. (for instance tomatoes), Liliaceae sp., Asteraceae sp. (for instance lettuces), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp., Papilionaceae sp. (for instance peas), Rosaceae sp. (for instance strawberries); major crops such as Graminae sp. (for instance maize, lawn or cereals such as wheat, rice, barley and triticale), Asteraceae sp. (for instance sunflower), Cruciferae sp. (for instance colza), Fabacae sp. (for instance peanuts), Papilionaceae sp. (for instance soybean), Solanaceae sp. (for instance potatoes), Chenopodiaceae sp. (for instance beetroots) horticultural and forest crops; as well as genetically modified homologues of these crops.

Among the diseases of plants or crops that can be controlled by the method according to the invention, mention may be made of:

Powdery mildew diseases such as:

-   -   Blumeria diseases, caused for example by Blumeria graminis;     -   Podosphaera diseases, caused for example by Podosphaera         leucotricha;     -   Sphaerotheca diseases, caused for example by Sphaerotheca         fuliginea;     -   Uncinula diseases, caused for example by Uncinula necator;

Rust diseases such as:

-   -   Gymnosporangium diseases, caused for example by Gymnosporangium         sabinae;     -   Hemileia diseases, caused for example by Hemileia vastatrix;     -   Phakopsora diseases, caused for example by Phakopsora pachyrhizi         or Phakopsora meibomiae;     -   Puccinia diseases, caused for example by Puccinia recondita;     -   Uromyces diseases, caused for example by Uromyces         appendiculatus;

Oomycete diseases such as:

-   -   Bremia diseases, caused for example by Bremia lactucae;     -   Peronospora diseases, caused for example by Peronospora pisi         or P. brassicae;     -   Phytophthora diseases, caused for example by Phytophthora         infestans;     -   Plasmopara diseases, caused for example by Plasmopara viticola;     -   Pseudoperonospora diseases, caused for example by         Pseudoperonospora humuli or Pseudoperonospora cubensis;     -   Pythium diseases, caused for example by Pythium ultimum;

Leafspot, leaf blotch and leaf blight diseases such as:

-   -   Alternaria diseases, caused for example by Alternaria solani;     -   Cercospora diseases, caused for example by Cercospora beticola;     -   Cladiosporum diseases, caused for example by Cladiosporium         cucumerinum;     -   Cochliobolus diseases, caused for example by Cochliobolus         sativus;     -   Colletotrichum diseases, caused for example by Colletotrichum         lindemuthanium;     -   Cycloconium diseases, caused for example by Cycloconium         oleaginum;     -   Diaporthe diseases, caused for example by Diaporthe citri;     -   Elsinoe diseases, caused for example by Elsinoe fawcettii;     -   Gloeosporium diseases, caused for example by Gloeosporium         laeticolor;     -   Glomerella diseases, caused for example by Glomerella cingulata;     -   Guignardia diseases, caused for example by Guignardia bidwelli;     -   Leptosphaeria diseases, caused for example by Leptosphaeria         maculans; Leptosphaeria nodorum;     -   Magnaporthe diseases, caused for example by Magnaporthe grisea;     -   Mycosphaerella diseases, caused for example by Mycosphaerella         graminicola; Mycosphaerella arachidicola; Mycosphaerella         fijiensis;     -   Phaeosphaeria diseases, caused for example by Phaeosphaeria         nodorum;     -   Pyrenophora diseases, caused for example by Pyrenophora teres;     -   Ramularia diseases, caused for example by Ramularia collo-cygni;     -   Rhynchosporium diseases, caused for example by Rhynchosporium         secalis;     -   Septoria diseases, caused for example by Septoria apii or         Septoria lycopercisi;     -   Typhula diseases, caused for example by Typhula incamata;     -   Venturia diseases, caused for example by Venturia inaequalis;

Root and stem diseases such as:

-   -   Corticium diseases, caused for example by Corticium graminearum;     -   Fusarium diseases, caused for example by Fusarium oxysporum;     -   Gaeumannomyces diseases, caused for example by Gaeumannomyces         graminis;     -   Rhizoctonia diseases, caused for example by Rhizoctonia solani;     -   Tapesia diseases, caused for example by Tapesia acuformis;     -   Thielaviopsis diseases, caused for example by Thielaviopsis         basicola;

Ear and panicle diseases such as:

-   -   Alternaria diseases, caused for example by Alternaria spp.     -   Aspergillus diseases, caused for example by Aspergillus flavus;     -   Cladosporium diseases, caused for example by Cladosporium spp.     -   Claviceps diseases, caused for example by Claviceps purpurea;     -   Fusarium diseases, caused for example by Fusarium culmorum;     -   Gibberella diseases, caused for example by Gibberella zeae;     -   Monographella diseases, caused for example by Monographella         nivalis;

Smut and bunt diseases such as:

-   -   Sphacelotheca diseases, caused for example by Sphacelotheca         reiliana;     -   Tilletia diseases, caused for example by Tilletia caries;     -   Urocystis diseases, caused for example by Urocystis occulta;     -   Ustilago diseases, caused for example by Ustilago nuda;

Fruit rot and mould diseases such as:

-   -   Aspergillus diseases, caused for example by Aspergillus flavus:     -   Botrytis diseases, caused for example by Botrytis cinerea;     -   Penicillium diseases, caused for example by Penicillium         expansum;     -   Sclerotinia diseases, caused for example by Sclerotinia         sclerotiorum;     -   Verticilium diseases, caused for example by Verticilium         alboatrum;

Seed and soilborne decay, mould, wilt, rot and damping-off diseases:

-   -   Fusarium diseases, caused for example by Fusarium culmorum;     -   Phytophthora diseases, caused for example by Phytophthora         cactorum;     -   Pythium diseases, caused for example by Pythium ultimum;     -   Rhizoctonia diseases, caused for example by Rhizoctonia solani;     -   Sclerotium diseases, caused for example by Sclerotium rolfsii;     -   Microdochium diseases, caused for example by Microdochium         nivale;

Canker, broom and dieback diseases such as:

-   -   Nectria diseases, caused for example by Nectria galligena;

Blight diseases such as:

-   -   Monilinia diseases, caused for example by Monilinia laxa;

Leaf blister or leaf curl diseases such as:

-   -   Taphrina diseases, caused for example by Taphrina deformans;

Decline diseases of wooden plants such as:

-   -   Esca diseases, caused for example by Phaemoniella clamydospora;     -   Eutypa dyeback, caused for example by Eutypa late;     -   Dutch elm disease, caused for example by Ceratocystsc ulmi;

Diseases of flowers and Seeds such as:

-   -   Botrytis diseases, caused for example by Botrytis cinerea;

Diseases of tubers such as:

-   -   Rhizoctonia diseases, caused for example by Rhizoctonia solani.

Among the damaging pests or insects that can be controlled at any development stage according to the insecticide method of the invention, mention may be made to:

-   -   the order of the Anoplura (Phthiraptera), for example, Damalinia         spp., Haematopinus spp., Linognathus spp., Pediculus spp.,         Trichodectes spp.;     -   the class of the Arachnida, for example, Acarus siro, Aceria         sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Argas spp.,         Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes         spp., Dermanyssus gallinae, Eotetranychus spp., Epitrimerus         pyri, Eutetranychus spp., Eriophyes spp., Hemitarsonemus spp.,         Hyalomma spp., Ixodes spp., Latrodectus mactans, Metatetranychus         spp., Oligonychus spp., Ornithodoros spp., Panonychus spp.,         Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes         spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp.,         Scorpio maurus, Stenotarsonemus spp., Tarsonemus spp.,         Tetranychus spp., Vasates lycopersici;     -   the class of the Bivalva, for example, Dreissena spp.;     -   the order of the Chilopoda, for example, Geophilus spp.,         Scutigera spp.;     -   the order of the Coleoptera, for example, Acanthoscelides         obtectus, Adoretus spp., Agelastica alni, Agriotes spp.,         Amphimallon solstitialis, Anobium punctatum, Anoplophora spp.,         Anthonomus spp., Anthrenus spp., Apogonia spp., Atomaria spp.,         Attagenus spp., Bruchidius obtectus, Bruchus spp.,         Ceuthorhynchus spp., Cleonus mendicus, Conoderus spp.,         Cosmopolites spp., Costelytra zealandica, Curculio spp.,         Cryptorhynchus lapathi, Dermestes spp., Diabrotica spp.,         Epilachna spp., Faustinus cubae, Gibbium psylloides,         Heteronychus arator, Hylamorpha elegans, Hylotrupes bajulus,         Hypera postica, Hypothenemus spp., Lachnosterna consanguinea,         Leptino-tarsa decemlineata, Lissorhoptrus oryzophilus, Lixus         spp., Lyctus spp., Meligethes aeneus, Melolontha melolontha,         Migdolus spp., Monochamus spp., Naupactus xanthographus, Niptus         hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis,         Otiorrhynchus sulcatus, Oxycetonia jucunda, Phaedon cochleariae,         Phyllophaga spp., Popillia japonica, Premnotrypes spp.,         Psylliodes chrysocephala, Ptinus spp., Rhizobius ventralis,         Rhizopertha dominica, Sitophilus spp., Sphenophorus spp.,         Sternechus spp., Symphyletes spp., Tenebrio molitor, Tribolium         spp., Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus         spp.     -   the order of the Collembola, for example, Onychiurus armatus;     -   the order of the Dermaptera, for example, Forficula auricularia;     -   the order of the Diplopoda, for example, Blaniulus guttulatus;     -   the order of the Diptera, for example, Aedes spp., Anopheles         spp., Bibio hortulanus, Calliphora erythrocephala, Ceratitis         capitata, Chrysomyia spp., Cochliomyia spp., Cordylobia         anthropophaga, Culex spp., Cuterebra spp., Dacus oleae,         Dermatobia hominis, Drosophila spp., Fannia spp., Gastrophilus         spp., Hylemyia spp., Hyppobosca spp., Hypoderma spp., Liriomyza         spp., Lucilia spp., Musca spp., Nezara spp., Oestrus spp.,         Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Stomoxys spp.,         Tabanus spp., Tannia spp., Tipula paludosa, Wohlfahrtia spp;     -   the class of the Gastropoda, for example, Arion spp.,         Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp.,         Lymnaea spp., Oncomelania spp., Succinea spp.;     -   the class of the helminths, for example, Ancylostoma duodenale,         Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma         spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia         timori, Bunostomum spp., Chabertia spp., Clonorchis spp.,         Cooperia spp., Dicrocoelium spp, Dictyocaulus filaria,         Diphyllobothrium latum, Dracunculus medinensis, Echinococcus         granulosus, Echinococcus multilocularis, Enterobius         vermicularis, Faciola spp., Haemonchus spp., Heterakis spp.,         Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp.,         Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus,         Ostertagia spp., Paragonimus spp., Schistosomen spp,         Strongyloides fuelleborni, Strongyloides stercoralis,         Stronyloides spp., Taenia saginata, Taenia solium, Trichinella         spiralis, Trichinella nativa, Trichinella britovi, Trichinella         nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp.,         Trichuris trichuria, Wuchereria bancrofti;     -   Protozoa, such as Eimeria;     -   the order of the Heteroptera, for example, Anasa tristis,         Antestiopsis spp., Blissus spp., Calocoris spp., Campylomma         livida, Cavelerius spp., Cimex spp., Creontiades dilutus,         Dasynus piperis, Dichelops furcatus, Diconocoris hewetti,         Dysdercus spp., Euschistus spp., Eurygaster spp., Heliopeltis         spp., Horcias nobilellus, Leptocorisa spp., Leptoglossus         phyllopus, Lygus spp., Macropes excavatus, Miridae, Nezara spp.,         Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp.,         Psallus seriatus, Pseudacysta persea, Rhodnius spp.,         Sahlbergella singularis, Scotinophora spp., Stephanitis nashi,         Tibraca spp., Triatoma spp;     -   the order of the Homoptera, for example, Acyrthosipon spp.,         Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobus         barodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui,         Aonidiella spp., Aphanostigma piri, Aphis spp., Arboridia         apicalis, Aspidiella spp., Aspidiotus spp., Atanus spp.,         Aulacorthum solani, Bemisia spp., Brachycaudus helichrysii,         Brachycolus spp., Brevicoryne brassicae, Calligypona marginata,         Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae,         Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis         tegalensis, Chlorita onukii, Chromaphis juglandicola,         Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli,         Coccus spp., Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp.,         Diaphorina spp., Diaspis spp., Doralis spp., Drosicha spp.,         Dysaphis spp., Dysmicoccus spp., Empoasca spp., Eriosoma spp.,         Erythroneura spp., Euscelis bilobatus, Geococcus coffeae,         Homalodisca coagulate, Hyalopterus arundinis, lcerya spp.,         Idiocerus spp., Idioscopus spp., Laodelphax striatellus,         Lecanium spp., Lepidosaphes spp., Lipaphis erysimi, Macrosiphum         spp., Mahanarva fimbriolata, Melanaphis sacchari, Metcalfiella         spp., Metopolophium dirhodum, Monellia costalis, Monelliopsis         pecanis, Myzus spp., Nasonovia ribisnigri, Nephotettix spp.,         Nilaparvata lugens, Oncometopia spp., Orthezia praelonga,         Parabemisia myricae, Paratrioza spp., Parlatoria spp., Pemphigus         spp., Peregrinus maidis, Phenacoccus spp., Phloeomyzus         passerinii, Phorodon humuli, Phylloxera spp., Pinnaspis         aspidistrae, Planococcus spp., Protopulvinaria pyriformis,         Pseudaulacaspis pentagona, Pseudococcus spp., Psylla spp.,         Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Quesada         gigas, Rastrococcus spp., Rhopalosiphum spp., Saissetia spp.,         Scaphoides titanus, Schizaphis graminum, Selenaspidus         articulatus, Sogata spp., Sogatella furcifera, Sogatodes spp.,         Stictocephala festina, Tenalaphara malayensis, Tinocallis         caryaefoliae, Tomaspis spp., Toxoptera spp., Trialeurodes         vaporariorum, Trioza spp., Typhlocyba spp., Unaspis spp., Viteus         vitifolii;     -   the order of the Hymenoptera, for example, Diprion spp.,         Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.;     -   the order of the Isopoda, for example, Armadillidium vulgare,         Oniscus asellus, Porcellio scaber;     -   the order of the Isoptera, for example, Reticulitermes spp.,         Odontotermes spp.;     -   the order of the Lepidoptera, for example, Acronicta major,         Aedia leucomelas, Agrotis spp., Alabama argillacea, Anticarsia         spp., Barathra brassicae, Bucculatrix thurberiella, Bupalus         piniarius, Cacoecia podana, Capua reticulana, Carpocapsa         pomonella, Cheimatobia brumata, Chilo spp., Choristoneura         fumiferana, Clysia ambiguella, Cnaphalocerus spp., Earias         insulana, Ephestia kuehniella, Euproctis chrysorrhoea, Euxoa         spp., Feltia spp., Galleria mellonella, Helicoverpa spp.,         Heliothis spp., Hofmannophila pseudospretella, Homona magnanima,         Hyponomeuta padella, Laphygma spp., Lithocolletis blancardella,         Lithophane antennata, Loxagrotis albicosta, Lymantria spp.,         Malacosoma neustria, Mamestra brassicae, Mocis repanda, Mythimna         separate, Oria spp., Oulema oryzae, Panolis flammea,         Pectinophora gossypiella, Phyllocnistis citrella, Pieris spp.,         Plutella xylostella, Prodenia spp., Pseudaletia spp.,         Pseudoplusia includens, Pyrausta nubilalis, Spodoptera spp.,         Thermesia gemmatalis, Tinea pellionella, Tineola bisselliella,         Tortrix viridana, Trichoplusia spp.;     -   the order of the Orthoptera, for example, Acheta domesticus,         Blatta orientalis, Blattella germanica, Gryllotalpa spp.,         Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta         americana, Schistocerca gregaria;     -   the order of the Siphonaptera, for example, Ceratophyllus spp.,         Xenopsylla cheopis.     -   the order of the Symphyla, for example, Scutigerella immaculate;     -   the order of the Thysanoptera, for example, Baliothrips         biformis, Enneothrips flavens, Frankliniella spp., Heliothrips         spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips         cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips         spp.;     -   the order of the Thysanura, for example, Lepisma saccharine;     -   the phytoparasitic nematodes including for example, Anguina         spp., Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus         spp., Ditylenchus dipsaci, Globodera spp., Heliocotylenchus         spp., Heterodera spp., Longidorus spp., Meloidogyne spp.,         Pratylenchus spp., Radopholus similis, Rotylenchus spp.,         Trichodorus spp., Tylenchorhynchus spp., Tylenchulus spp.,         Tylenchulus semipenetrans, Xiphinema spp;     -   the beetles, such as Hylotrupes bajulus, Chlorophorus pilosis,         Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis,         Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus         brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis,         Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis,         Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus         capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus         minutus;     -   Hymenopterons, such as Sirex juvencus, Urocerus gigas, Urocerus         gigas taignus, Urocerus augur;     -   termites, such as Kalotermes flavicollis, Cryptotermes brevis,         Heterotermes indicola, Reticulitermes flavipes, Reticulitermes         santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis,         Zootermopsis nevadensis, Coptotermes formosanus;     -   Bristletails, such as Lepisma saccharina;     -   the order of the Acarina, for example, Argas persicus, Argas         reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus         domesticus, Ornithodorus moubat, Rhipicephalus sanguineus,         Trombicula alfreddugesi, Neutrombicula autumnalis,         Dermatophagoides pteronissimus, Dermatophagoides forinae;     -   the order of the Araneae, for example, Avicularlidae, Araneidae;     -   the order of the Opiliones, for example, Pseudoscorpiones         chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium;     -   the order of the Isopoda, for example, Oniscus asellus,         Porcellio scaber;     -   the order of the Diplopoda, for example, Blaniulus guttulatus,         Polydesmus spp.;     -   the order of the Chilopoda, for example, Geophilus spp.;     -   the order of the Zygentoma, for example, Ctenolepisma spp.,         Lepisma saccharine, Lepismodes inquilinus;     -   the order of the Blattaria, for example, Blatta orientalies,         Blattella germanica, Blattella asahinai, Leucophaea maderae,         Panchlora spp., Parcoblatta spp., Periplaneta australasiae,         Periplaneta americana, Periplaneta brunnea, Periplaneta         fuliginosa, Supella longipalpa;     -   the order of the Saltatoria, for example, Acheta domesticus;     -   the order of the Dermaptera, for example, Forficula auricularia;     -   the order of the Isoptera, for example, Kalotermes spp.,         Reticulitermes spp;     -   the order of the Psocoptera, for example, Lepinatus spp.,         Liposcelis spp;     -   the order of the Coleoptera, for example, Anthrenus spp.,         Attagenus spp., Dermestes spp.; Latheticus oryzae, Necrobia         spp., Ptinus spp., Rhizopertha dominica, Sitophilus granarius,         Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum.     -   the order of the Diptera, for example, Aedes aegypti, Aedes         albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora         erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus,         Culex pipiens, Culex tarsalis, Drosophila spp., Fannia         canicularis, Musca domestica, Phlebotomus spp., Sarcophaga         camaria, Simulium spp., Stomoxys calcitrans, Tipula paludosa;     -   the order of the Lepidoptera, for example, Achroia grisella,         Galleria mellonella, Plodia interpunctella, Tinea cloacella,         Tinea pellionella, Tineola bisselliella;     -   the order of the Siphonaptera, for example, Ctenocephalides         canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans,         Xenopsylla cheopis.     -   the order of the Hymenoptera, for example, Camponotus         herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus,         Monomorium pharaonis, Paravespula spp., Tetramorium caespitum;     -   the order of the Anoplura, for example, Pediculus humanus         capitis, Pediculus humanus corporis, Pemphigus spp., Phylloera         vastatrix, Phthirus pubis;     -   the order of the Heteroptera, for example, Cimex hemipterus,         Cimex lectularius, Rhodinus prolixus, Triatoma infestans.

The fungicide or insecticide composition according to the invention may also be used against fungal diseases or damaging insects liable to grow or attack on or inside timber. The term “timber” means all types of species of wood, and all types of working of this wood intended for construction, for example solid wood, high-density wood, laminated wood, and plywood. The method for treating timber according to the invention mainly consists in contacting one or more compounds according to the invention, or a composition according to the invention; this includes for example direct application, spraying, dipping, injection or any other suitable means.

The dose of active compound usually applied in the method of treatment according to the invention is generally and advantageously from 10 to 800 g/ha, preferably from 50 to 300 g/ha for applications in foliar treatment. The dose of active substance applied is generally and advantageously from 2 to 200 g per 100 kg of seed, preferably from 3 to 150 g per 100 kg of seed in the case of seed treatment.

It is clearly understood that the doses indicated herein are given as illustrative examples of the method according to the invention. A person skilled in the art will know how to adapt the application doses, notably according to the nature of the plant or crop to be treated.

The fungicide composition according to the invention may also be used in the treatment of genetically modified organisms with the compounds according to the invention or the agrochemical compositions according to the invention. Genetically modified plants are plants into genome of which a heterologous gene encoding a protein of interest has been stably integrated. The expression “heterologous gene encoding a protein of interest” essentially means genes which give the transformed plant new agronomic properties, or genes for improving the agronomic quality of the modified plant.

The compounds or mixtures according to the invention may also be used for the preparation of composition useful to curatively or preventively treat human or animal fungal diseases such as, for example, mycoses, dermatoses, trichophyton diseases and candidiases or diseases caused by Aspergillus spp., for example Aspergillus fumigatus.

The various aspects of the invention will now be illustrated with reference to the following tables of compounds and examples. The following tables illustrate in a non-limiting manner examples of compounds according to the invention.

In the following examples, M+1 (or M−1) means the molecular ion peak, plus or minus 1 a.m.u. (atomic mass unit) respectively, as observed in mass spectroscopy and M (Apcl+) means the molecular ion peak as it was found via positive atmospheric pressure chemical ionisation in mass spectroscopy.

In the following examples, the logP values were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a reversed-phase column (C 18), using the method described below:

Temperature: 40° C.; Mobile phases: 0.1% aqueous formic acid and acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile.

Calibration was carried out using linear alkan-2-ones (comprising 3 to 16 carbon atoms) with known logP values (determination of the logP values by the retention times using linear interpolation between two successive alkanones).

The lambda max values were determined in the maxima of the chromatographic signals using the UV spectra from 190 nm to 400 nm.

TABLE 1

log p No R2 R3 R1 R4 R5 R7 R8 (HCOOH) 1.1 Me Et H Me Me Cl Cl 2.12 1.2 Me Et H Me Me —CH═CH—C(Cl)═CH— 2.29 1.3 Me iPr H Me Me Cl Cl 2.18 1.4 Me Et H Me Me tBu Cl 2.76 1.5 Me Et H Me Me CF3 Cl 2.15 1.6 Me Et H Me Me Cl Br 2.00 1.7 —CH2CH2CH2CH2CH2— H Me Me Cl Cl 2.23 1.8 Me Et H Me Me —CH═CH—CH═CH— 1.89 1.9 Me iPr H Me Me iPr Cl 2.57 1.10 Me iPr H Me Me CF3 Cl 2.29 1.11 Me iPr H Me Me Cl Br 2.22 1.12 Me Et H Me Me Me Cl 1.98 1.13 Me iPr H Me Me Me Cl 2.14 1.14 Me iPr H Me Me Cl H 1.70 1.15 Me n-Pr H Me Me —CH═CH—C(Cl)═CH— 2.46 1.16 Me Et H Me Me Me CMe═NO-t-Bu 2.80 1.17 Me Et H Me Me Cl Me 1.80 1.18 Me Et H Me Me Cl H 1.60 1.19 Me Et H Me Me Me CMe═NOMe 1.97 1.20 Me Et H Me Me iPr Cl 2.52 1.21 Me Et H Me Me Me CMe═NO—CH2CH═CH2 2.33 1.22 —CH2CH2CH2CH2CH(CH3)— H Me Me Cl Cl 2.44 1.23 Me iPr H Me Me Cl Me 1.94 1.24 Me Et H Me Me Me CMe═NOCH(Me)Ph 2.87 1.25 H —CH2CH2CH2CH2— Me Me Cl Cl 1.97 1.26 —CH2CH2CH2CH2— H Me Me Cl Cl 2.12 1.27 Me Et H Me Me Me Ac 1.50 1.28 Me iPr H Me H Cl Cl 2.09 1.29 Me n-Pr H Me Me —CH═CH—CH═CH— 2.04 1.30 —CH2CH2—O—CH2CH2— H Me Me Cl Cl 1.95 1.31 Me Me H Me Me Cl Me 1.69 1.32 H —CH2CH2CH2— Me Me Cl Cl 1.93 1.33 Me Et H Me H Me Me 1.65 1.34 Me iPr H Me H Me Me 1.66 1.35 Me iPr H Me Me Me nPr 2.29 1.36 Me Et H Me Me Me nPr 2.22 1.37 Me iPr H Me Me Me Me 1.98 1.38 Me Et H Me Me Me Me 1.87 1.39 Me Et H Me H Cl Cl 1.99 1.40 Me Et H Me Me Me CMe═NOH 1.55 1.41 Me iPr H Me Me Me CMe═NOH 1.66 1.42 Me Et H Me Me CHO Cl 1.46 1.43 Me Et H Me Me CH═NOMe Cl 1.93 1.44 Me Et H Me Me CH═NO-t-Bu Cl 2.65 1.45 Me Et H Me Me CH═NO—CH2CH═CH2 Cl 2.26 1.46 Me Et H Me Me CH═NO-Et Cl 2.17 1.47 Me Et H Me Me CH═NO—CH2-Ph Cl 2.51 1.48 Me Et H Me Me CMe═NOCH(Me)Ph Cl 2.75 1.49 Me Et H Me Me CH═NO—CH2-(4-t-Bu)-Ph Cl 3.46 1.50 Me Et H Me Me CH═NO—CH2-(4-NO2)-Ph Cl 2.60 1.51 Me Et H Me Me CH═NO—CH2-(3-Me)-Ph Cl 2.84 1.52 Me Et H Me Me CH═NO—CH2-(3-Cl)-Ph Cl 2.86 1.53 Me Et H Me Me CH═NO—CH2-(4-CF3)-Ph Cl 3.01 1.54 Me Et H Me Me CH═NO—CH2-(3-CF3)-Ph Cl 2.97 1.55 Me Et H Me Me Cl 4-Cl-Ph 2.80 1.56 Me iPr H Me Me Cl 4-Cl-Ph 3.00 1.57 Me Et H Me Me Cl CH═NOMe 2.04 1.58 Me Et H Me Me Cl CH═NO—CH2CH═CH2 2.32 1.59 Me Et H Me Me Cl CH═NO—CH2-Ph 2.64 1.60 Me Et H Me Me Ph H 2.18 1.61 Me iPr H Me Me Ph H 2.25 1.62 Me Et H Me Me Cl CHO 1.68 1.63 Me Et H Me Me CH═NOH Cl 1.53 1.64 Me iPr H Me Me tBu Cl 2.79 1.65 —CH2CH2CH2CH2CH2— H Me Me tBu Cl 3.05 1.66 —CH2CH2CH2CH2CH2— H Me Me Cl 4-Cl-Ph 2.97 1.67 Me Et H Me Me —CCl═CH—CH═CH 2.17 1.68 —CH2CH2CH2CH2CH2— H Me Me —CCl═CH—CH═CH 2.34 1.69 Me nPr H Me Me —CCl═CH—CH═CH 2.29 1.70 Me iPr H Me Me —CCl═CH—CH═CH 2.40 1.71 Me Et H Me Me tBu Br 2.78 1.72 Me Et H Me Me CN Cl 1.74 1.73 Me Et H Me Me Cl tBu 2.87 1.74 Me Et H Me Me H tBu 2.18 1.75 Me Et H Me Me tBu H 2.26

TABLE 2

logP No R1 R2 R3 R4 R5 R9 (HCOOH) 2.1 H Me i-Pr Me H i-Pr 1.77 2.2 H Me Et Me H i-Pr 1.57 2.3 H Me Et Me Me i-Pr 1.74 2.4 H Me i-Pr Me Me i-Pr 1.89 2.5 H Me Et Me Me Cl 1.56 2.6 H Me i-Pr Me Me Cl 1.67 2.7 H Me Et Me H t-Bu 2.04

TABLE 3

logP No R1 R2 R3 R4 R5 R10 (HCOOH) 3.1 H Me i-Pr Me Me CF3 1.84 3.2 H Me Et Me Me CF3 1.78 3.3 H Me Et Me Me Ph 1.93 3.4 H Me Et Me Me 2-F-6-OMe-Ph 1.87 3.5 H Me Et Me Me 2-F-Ph 1.98 3.6 H Me i-Pr Me Me Ph 2.00 3.7 H Me Et Me Me 3-F-4-F-Ph 2.08 3.8 H Me Et Me Me 4-OCF₃-Ph 2.35 3.9 H Me i-Pr Me Me 4-OCF₃-Ph 2.48 3.10 H Me Et Me Me 2-F-4-CF₃-Ph 2.33 3.11 H Me i-Pr Me Me 2-F-4-CF₃-Ph 2.43 3.12 H Me Et Me Me 4-SO₂Me-Ph 1.52 3.13 H Me i-Pr Me Me 3-F-4-F-Ph 2.28 3.14 H Me i-Pr Me Me 2-F-Ph 2.22 3.15 H Me i-Pr Me Me 2-F-6-OMe-Ph 2.11 3.16 H Me i-Pr Me Me 4-SO₂Me-Ph 1.69 3.17 H Me i-Pr Me Me 2-Cl-Ph 2.11 3.18 H Me i-Pr Me Me SMe 1.82 3.19 H Me i-Pr Me Me i-Pr 1.69 3.20 H Me Et Me Me 2-Cl-Ph 2.05 3.21 H Me Et Me Me SMe 1.69 3.22 H Me Et Me Me i-Pr 1.61 3.23 H Me Et Me Me cyclo-Pr 1.50 3.24 H Me Et Me Me 3-Cl-4-F-Ph 2.13 3.25 H Me i-Pr Me Me 4-MeO-Ph 2.02 3.26 H Me i-Pr Me Me 3-MeO-Ph 2.06 3.27 H Me i-Pr Me Me 3-Me-Ph 2.12 3.28 H Me Et Me Me 4-NO₂-Ph 1.92 3.29 H Me Et Me Me 4-MeO-Ph 1.93 3.30 H Me Et Me Me 3-MeO-Ph 2.02 3.31 H Me Et Me Me 3-Me-Ph 2.06 3.32 H Me i-Pr Me Me cyclo-Pr 1.57 3.33 H Me i-Pr Me Me 4-NO₂-Ph 2.05 3.34 H Me i-Pr Me Me 3-Cl-4-F-Ph 2.27 3.35 H —CH2CH2CH2CH2— Me Me 4-OCF₃-Ph 2.64 3.36 H —CH2CH2CH2CH2— Me Me 2-F-4-CF₃-Ph 2.61 3.37 H —CH2CH2CH2CH2— Me Me 3-Me-Ph 2.21 3.38 H —CH2CH2CH2CH2— Me Me 2-F-Ph 2.19 3.39 H —CH2CH2CH2CH2— Me Me 2-Cl-Ph 2.21 3.40 H —CH2CH2CH2CH2— Me Me SMe 1.89 3.41 H —CH2CH2CH2CH2— Me Me i-Pr 1.73 3.42 H —CH2CH2CH2CH2— Me Me 3-Cl-4-F-Ph 2.43 3.43 H —CH2CH2CH2CH2— Me Me cyclo-Pr 1.65 3.44 —CH2CH2CH2— H Me Me CF3 1.59

The following examples illustrate in a non-limiting manner the preparation and efficacy of the compounds of formula (I) according to the invention.

PREPARATION EXAMPLE 1 Process (a)—compound (IV) to compound (II): 4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylaniline-intermediate (II-1)

1.3 g (33 mmol) sodium hydride (60% in oil) were added portionwise to a solution of 4.1 g (30.0 mmol) of 4-amino-2,5-dimethylphenol in 30 ml of dimethylformamide. After the gas evolution has stopped, 5.6 g (30 mmol) of 2,4,5-trichloro-1,3-thiazole were added and the reaction mixture was stirred for 1 h at 100° C. At ambient temperature 0.5 ml methanol, 10 ml of water and 100 ml of ethyl acetate were added successively. The organic layer was separated, the watery layer extracted with ethyl acetate and the combined organic layers were dried over magnesium sulfate. Concentration in vacuo and column chromatographie (petroleum ether/acetone 4/1) yielded 4.8 g (16.6 mmol, 55%) of 4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylaniline log P (pH=2.3)=3.4

PREPARATION EXAMPLE 2 Process (b2)—compound (II) to compound (I): N′-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide-compound 1.1

To a mixture of 2.0 g (6.9 mmol) of 4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylaniline in 2.5 ml toluene a solution of 9.7 mmol of N-(dimethoxymethyl)-N-methylethanamine (60% in methanol) was added. The reaction mixture was stirred for 16 hrs at 105° C. The reaction mixture was concentrated in vacuo. Column chromatographie (gradient: cyclohexane->ethyl acetate) yielded 2.4 g (6.7 mmol) 97% of N′-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide; log P (pH 2.3)=2.04

PREPARATION EXAMPLE 3 Process (b3)—compound (II) to compound (I): N′-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methlimidoformamide-compound 1.1

To a mixture of 2.0 g (6.9 mmol) of 4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylaniline and 11.3 ml (0.13 mol) of trimethoxymethane 0.12 g (0.7 mmol) of p-toluene sulfonic acid were added. The reaction mixture was refluxed for 16 hrs and concentrated in vacuo. The crude product was solved in 12 ml of toluene and 0.82 g (13.8 mmol) N-methylethanamine were added. The reaction mixture was stirred for 16 hrs at 50° C. The reaction mixture was concentrated in vacuo. Column chromatographie (gradient: petroleum ether->methyl-tert. butyl ether) yielded 2.3 g (6.3 mmol) 91% of N′-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide; log P (pH 2.3)=2.04

PREPARATION EXAMPLE 4 Process (b1)—compound (II) to compound (I): 4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethyl-N-[piperidin-2-lidene]aniline-compound 1.25

A solution of 0.2 g (1.5 mmol) of phosphoric trichloride in 5 ml toluene was added to a mixture of 0.3 g (3.0 mmol) of piperidin-2-one, the exothermic reaction was stirred for 2 hrs at ambient temperature. Then a solution of 0.43 g (1.5 mmol) of 4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylaniline in 5 ml of toluene was added and the reaction mixture was refluxed for 5 hrs. At ambient temperature 5 ml of a 10% aqueous solution of sodium hydroxide was added. Seperation of the layers, extraction of the watery layer with 10 ml of toluene, drying over magnesium sulfate, concentration in vacuo and Column chromatographie (gradient: cyclohexane->ethyl acetate) yielded 0.55 g (1.5 mmol) 99% of 4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethyl-N-[piperidin-2-lidene]aniline; log P (pH 2.3)=1.97

PREPARATION EXAMPLE 5 Process (c)—compound (I) to compound (I): N′-(4-{([5-(N-allylethanimidoyl)-4-methyl-1,3-thiazol-2-yl]oxyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide-compound 1.21

A solution of 0.3 g (0.87 mmol) of N′-{4-[(5-acetyl-4-methyl-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide and 0.095 g (0.87 mmol) of 3-(aminooxy)prop-1-ene hydrochloride in a solvent mixture of 10 ml of methanol and 3 ml of water was stirred at ambient temperature for 5 days. Then the mixture was diluted with water and dichloromethane was added. Separation of the layers, extraction of the water phase with dichloromethane, drying of the organic layer over sodium sulfate end evaporation of the solvent yielded 0.14 g (0.29 mmol) 33% of N′-(4-{[5-(N-allylethanimidoyl)-4-methyl-1,3-thiazol-2-yl]oxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide as a mixture of two stereoisomers; log P (pH 2.3)=2.15 and 2.33.

PREPARATION EXAMPLE 5 Process (b3)—compound (III) to compound (IX): N-ethyl-N′-(4-hydroxy-2,5-dimethylphenyl)-N-methylimidoformamide-intermediate (IX-a)

To a mixture of 10.0 g (73 mmol) of 4-amino-2,5-dimethylphenol and 73 ml (0.84 mol) of trimethoxymethane 0.73 g (4.2 mmol) of p-toluene sulfonic acid were added and the mixture was heated to reflux for 2 hours. Then the volatiles were removed in vacuo and the residue was dissolved in 73 ml of toluene and 12.9 g (217 mmol) N-methylethanamine were added. The reaction mixture was heated to 50° C. for 20 hrs and concentrated in vacuo. Column chromatographie (gradient: cyclohexane->ethyl acetate) yielded 9.17 g (44 mmol) 55% of N-ethyl-N′-(4-hydroxy-2,5-dimethylphenyl)-N-methylimidoformamide; log P (pH 2.3)=0.41.

PREPARATION EXAMPLE 6 Process (a)—compound (IV) and compound (IX) to compound (I): N′-{4-[(5-chloro-4-formyl-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide-compound 1.42

To a solution of 3.57 g (17 mmol) of N-ethyl-N′-(4-hydroxy-2,5-dimethylphenyl)-N-methylimidoformamide in 60 ml of DMF were added 2.51 g (18 mmol) of potassium carbonate and the mixture was stirred at ambient temperature for 30 min. Then 3.00 g (16.5 mmol) of 2,5-dichloro-1,3-thiazole-4-carbaldehyde were added and the mixture was stirred at ambient temperature for 7 days. Then the reaction mixture was poured on water, dichloromethane and some NaCl was added, layers were separated, the water layer was extracted with dichloromethane, the organic phase was dried over sodium sulfate and evaporated. Column chromatographie (gradient: dichloromethane->methanol) yielded 4.40 g (12.5 mmol) 67% of N′-{4-[(5-chloro-4-formyl-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide log P (pH 2.3)=1.51

PREPARATION EXAMPLE 7 Process (c): N′-[4-({4-[(tert-butoxyimino)methyl]-5-chloro-1,3-thiazol-2-yl}oxy)-2,5-dimethylphenyl]-N-ethyl-N-methylimidoformamide-compound 1.44

A solution of 0.23 g (0.50 mmol) of N′-{4-[(5-chloro-4-formyl-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide and 63 mg (0.50 mmol) of 2-(aminooxy)-2-methylpropane hydrochloride in a solvent mixture of 10 ml of methanol and 3 ml of water was stirred at ambient temperature for 5 days. Evaporation of the solvents and column chromatography of the crude mixture (gradient cyclohexane->ethyl acetate) yielded 130 mg (0.37 mmol) 61% of N′-[4-({4-[(tert-butoxyimino)methyl]-5-chloro-1,3-thiazol-2-yl}oxy)-2,5-dimethylphenyl]-N-ethyl-N-methylimidoformamide. Log P (pH 2.3)=2.65

EFFICACY EXAMPLE A In vivo Preventive Test on Puccinia recondita f. Sp. tritici (Wheat Brown Rust)

Solvent: 50 parts by weight of N,N-dimethylacetamid Emulsifier:  1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for preventive activity, young plants are inoculated with a spore suspension of Puccinia recondita in a 0.1% strength aqueous agar solution. After the spray coating has dried on, the plants are sprayed with the preparation of active compound at the stated rate of application. The plants remain for 24 hours in an incubation cabinet at 20° C. and a relative atmospheric humidity of 100%.

The plants are placed in a greenhouse at a temperature of approximately 20° C. and a relative atmospheric humidity of approximately 80% to promote the development of rust pustules.

The test is evaluated 10 days after the inoculation. 0% means an efficacy which corresponds to that of the control, while an efficacy of 100% means that no disease is observed.

In this test the following compounds according to the invention showed an efficacy of 70% or even higher at a concentration of 1000 ppm of active ingredient: 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 1.10, 1.11, 1.12, 1.13, 1.15, 1.17, 1.18, 1.20, 1.23, 1.28, 1.29, 1.63, 1.71, 1.72, 1.73, 1.74, 1.75, 2.2, 2.3, 2.4, 2.7, 3.1, 3.2.

EFFICACY EXAMPLE B In Vivo Preventive Test on Erysiphe gramini (Powdery Mildew on Barley)

Solvent: 50 parts by weight of N,N-dimethylacetamid

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for preventive activity, young plants are sprayed with the preparation of active compound or active compound combination at the stated rate of application.

After the spray coating has dried on, the plants are dusted with spores of Erysiphe graminis f. sp. hordei.

The plants are placed in a greenhouse at a temperature of approximately 20° C. and a relative atmospheric humidity of approximately 80% to promote the development of mildew pustules.

The test is evaluated 7 days after the inoculation. 0% means an efficacy which corresponds to that of the control, while an efficacy of 100% means that no disease is observed.

In this test the following compounds according to the invention showed an efficacy of 70% or even higher at a concentration of 1000 ppm of active ingredient: 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 1.10, 1.11, 1.12, 1.13, 1.17, 1.18, 1.20, 1.23, 1.28, 1.29, 2.2, 2.3, 2.4, 3.1, 3.2.

EFFICACY EXAMPLE C In Vivo Protective Test on Alternaria solani (Leaf Spot of Tomato)

Solvent: 49 parts by weight of N,N-dimethylformamide

Emulsifier: 1 part by weight of alkylarylpolyglycolether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for protective activity, young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Alternaria solani. The plants remain for one day in an incubation cabinet at approximately 20° C. and a relative atmospheric humidity of 100%. Then the plants are placed in an incubation cabinet at approximately 20° C. and a relative atmospheric humidity of 96%.

The test is evaluated 7 days after the inoculation. 0% means an efficacy which corresponds to that of the control while an efficacy of 100% means that no disease is observed.

In this test, invention related compounds of the following formula revealed an efficacy of 70% or higher at a concentration of 500 ppm of active ingredient: 1.1, 1.2, 1.3, 1.4, 1.5, 1.7, 1.7, 1.8, 1.9, 1.12, 1.13, 1.14, 1.16, 1.17, 1.19, 1.20, 1.21, 1.24, 1.27, 1.63, 1.64, 1.65, 1.66, 1.70, 1.71, 1.74, 2.3, 2.7, 3.2, 3.20, 3.21, 3.24, 3.31, 3.34, 3.35, 3.39.

EFFICACY EXAMPLE D In Vivo Protective Test on Podosphaera leucotricha (Apples)

Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide Emulsifier:   1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for protective activity, young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of the causal agent of apple mildew (Podosphaera leucotricha). The plants are then placed in a greenhouse at approximately 23° C. and a relative atmospheric humidity of approximately 70%.

The test is evaluated 10 days after the inoculation. 0% means an efficacy which corresponds to that of the control, while an efficacy of 100% means that no disease is observed.

In this test the compounds according to the invention of the following structures showed efficacy of 70% or even higher at a concentration of 100 ppm of active ingredient: 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 1.10, 1.11, 1.12, 1.15, 1.17, 1.18, 1.71, 1.72, 1.74, 1.75, 2.3, 2.7.

EFFICACY EXAMPLE E In Vivo Protective Test on Sphaerotheca fuliginea (Cucumbers)

Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide Emulsifier:   1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for protect activity, young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Sphaerotheca fuliginea. The plants are then placed in a greenhouse at approximately 23° C. and a relative atmospheric humidity of approximately 70%.

The test is evaluated 7 days after the inoculation. 0% means an efficacy which corresponds to that of the control, while an efficacy of 100% means that no disease is observed.

In this test the compounds according to the invention of the following structures showed efficacy of 70% or even higher at a concentration of 100 ppm of active ingredient: 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 1.10, 1.11, 1.12, 1.15, 1.18, 1.21, 1.63, 2.3.

EFFICACY EXAMPLE F In Vivo Protective Test on Uromyces appendiculatus (Beans)

Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide Emulsifier:   1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for protective activity, young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of the causal agent of bean rust (Uromyces appendiculatus) and then remain for 1 day in an incubation cabinet at approximately 20° C. and a relative atmospheric humidity of 100%.

The plants are then placed in a greenhouse at approximately 21° C. and a relative atmospheric humidity of approximately 90%.

The test is evaluated 10 days after the inoculation. 0% means an efficacy which corresponds to that of the control, while an efficacy of 100% means that no disease is observed.

In this test the compounds according to the invention of the following structures showed efficacy of 70% or even higher at a concentration of 100 ppm of active ingredient: 1.2, 1.71, 1.72, 1.74, 1.75, 2.7.

EFFICACY EXAMPLE G Myzus persicae—Test: (MYZUPE Spray Application)

Solvent:  78 parts by weight acetone 1.5 parts by weight dimethylformamide Wetting agent: 0.5 parts by weight alkylarylpolyglcolether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.

Chinese cabbage (Brassica pekinesis) leaf-disks infected with all instars of the green peach aphid (Myzus persicae), are sprayed with a preparation of the active ingredient at the desired concentration.

After the specified period of time, mortality in % is determined. 100% means that all aphids have been killed; 0% means that none of the aphids have been killed.

In this test for example, the following compounds from the preparation examples showed good activity: 1.25

EFFICACY EXAMPLE H Heliotis virescens—Test on Heliotis virescens (HELIVI Spray Application)

Solvent:  78 parts by weight acetone 1.5 parts by weight dimethylformamide Wetting agent 0.5 parts by weight alkylarylpolyglcolether

To produce a suitable preparation of the active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and emulsifier, and the concentrate is dilutes with emulsifier-containing water to the desired concentration.

Soybean (Glycine max.) leaf sections are sprayed with a preparation of the active ingredient of the desired concentration. Once dry, the leaf sections are infested with eggs of cotton bollworm (Heliotis virescens).

After the specified period of time, mortality in % is determined. 100% means that all eggs have been killed and 0% means that none of the eggs have been killed.

In this test for example, the following compounds from the preparation examples showed good activity: 1.11, 1.23, 1.25, 1.26. 

1. A phenyl-amidine derivative of formula (I):

wherein R¹ represents H, a substituted or non substituted C₁-C₁₂-alkyl, a substituted or non substituted C₂-C₁₂-alkenyl, a substituted or non substituted C₂-C₁₂-alkynyl, SH or a substituted or non substituted S—C₁-C₁₂-alkyl R² represents a substituted or non substituted C₁-C₁₂-alkyl R³ represents a substituted or non substituted C₂-C₁₂-alkyl, substituted or non substituted C₃-C₆-cycloalkyl, substituted or non substituted C₂-C₁₂-alkenyl, substituted or non substituted C₂-C₁₂-alkynyl, halogeno-C₁-C₁₂-alkyl; or R¹ and R², R¹ and R³ or R² and R³ can form together a substituted or non substituted 5- to 7-membered heterocycle; R⁴ represents a substituted or non substituted C₁-C₁₂-alkyl, a halogen atom, halogeno-C₁-C₁₂-alkyl, substituted or non substituted O—C₁-C₁₂-alkyl or cyano; R⁵ represents H, a substituted or non substituted C₁-C₁₂-alkyl, a halogen atom, halogeno-C₁-C₁₂-alkyl, substituted or non substituted O—C₁-C₁₂-alkyl or cyano; R⁶ represents a heterocycle selected in the group consisting of and

R⁷ represents H, halogen, nitro, cyano; substituted or non substituted phenyl, substituted or non substituted benzyl; C₁-C₈-alkyl, C₁-C₈-alkoxy, C₁-C₈-alkylthio, C₁-C₆-halogenalkyl, C₁-C₆-halogenalkoxy or C₁-C₆-halogenalkylthio; C₁-C₈-alkyl-S(O)_(m)R¹¹; C₁-C₈-alkyl-SO₂NR¹²R¹³; C₁-C₈-alkyl-COR¹⁴; —CR¹⁵═N—O—R¹⁶, S(O)_(m)R¹¹, SO₂NR¹²R¹³, COR¹⁴; R⁸ represents H, halogen, cyano; substituted or non substituted phenyl, substituted or non substituted benzyl; C₁-C₈-alkyl, C₁-C₈-alkoxy, C₁-C₈-alkylthio, C₁-C₆-halogenalkyl, C₁-C₆-halogenalkoxy or C₁-C₆-halogenalkylthio; C₁-C₈—COR¹⁴; —CR¹⁵═N—O—R¹⁶, COR¹⁴; R⁷ and R⁸ can form a carbocycle, which can be saturated, unsaturated or aromatic and substituted or non substituted by halogen, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, or C₁-C₄-alkoxyalkyl; R⁹ represents H, halogen, cyano; substituted or non substituted phenyl, substituted or non substituted benzyl; C₁-C₈-alkyl, C₁-C₈-alkoxy, C₁-C₈-alkylthio, C₁-C₆-halogenalkyl, C₁-C₆-halogenalkoxy or C₁-C₆-halogenalkylthio; C₁-C₈—COR¹⁴; —CR¹⁵═N—O—R¹⁶, COR¹⁴; R¹⁰ represents H, halogen, cyano; substituted or non substituted phenyl, substituted or non substituted benzyl, substituted or non substituted pyridyl; C₁-C₈-alkyl, C₁-C₈-alkoxy, C₁-C₈-alkylthio, C₁-C₆-halogenalkyl, C₁-C₆-halogen-alkoxy or C₁-C₆-halogenalkylthio; C₁-C₈—S(O)_(m)R¹¹; C₁-C₈—SO₂NR¹²R¹³; C₁-C₈—COR¹⁴; —CR¹⁵═N—O—R¹⁶, S(O)_(m)R¹¹, SO₂NR¹²R¹³, COR¹⁴; m represents 0, 1 or 2; R¹¹ represents C₁-C₈-alkyl, C₃-C₆-cycloalkyl; R¹² represents H, C₁-C₈-alkyl, C₃-C₆-cycloalkyl; R¹³ represents H, C₁-C₈-alkyl, C₃-C₆-cycloalkyl; R¹⁴ represents H, substituted or non substituted, branched or linear C₁-C₈-alkyl, C₁-C₈-alkoxy; R¹⁵ represents H, C₁-C₈-alkyl, C₃-C₆-cycloalkyl; R¹⁶ represents H, C₁-C₈-alkyl, C₃-C₆-cycloalkyl, C₁-C₈-alkoxy, substituted or non substituted benzyl; R¹² and R¹³ can form a 5- or 6-membered heterocycle, which can further comprise one or more heteroatoms selected in the group consisting of O, N, and S; R¹⁵ and R¹⁶ can form a heterocyclic 5- or 6-membered ring, optionally including at least one further heteroatom; as well as salt, an N-oxide, a metallic complexe, a metalloidic complexe and/or an optically active or geometric isomer thereof.
 2. A compound of formula (I) according to claim 1 wherein R¹ represents H, C₁-C₁₂-alkyl or SH; or R² represents methyl; or R³ represents C₂-C₁₂-alkyl, C₂-C₁₂-alkenyl; C₃-C₆-cycloalkyl; or R² and R³ can form together a substituted or non substituted 5- to 7-membered heterocycle; or R⁴ represents C₁-C₁₂-alkyl, a halogen atom or trifluoromethyl; or R⁵ represents H, C₁-C₁₂-alkyl, a halogen atom or trifluoromethyl; or R⁷ represents H, Cl, Br, I, nitro, cyano; phenyl; phenyl substituted by F, Cl, Br, I, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy; benzyl; benzyl substituted by F, Cl, Br, I, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy; C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-halogenalkyl, C₁-C₄-halogenalkoxy or C₁-C₄-halogenalkylthio; C₁-C₄—S(O)_(m)R¹¹; C₁-C₄—SO₂NR¹²R¹³; C₁-C₄—COR¹⁴; —CR¹⁵═N—O—R¹⁶, S(O)_(m)R¹¹, SO₂NR¹²R¹³, COR¹⁴; or R⁸ represents H, Cl, Br, I, cyano; phenyl; phenyl substituted by F, Cl, Br, I, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy; benzyl; benzyl substituted by F, Cl, Br, I, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy; C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-halo-genalkyl, C₁-C₄-halogenalkoxy or C₁-C₄-halogenalkylthio; C₁-C₄—COR¹⁴; —CR¹⁵═N—O—R¹⁶, COR¹⁴; or R⁷ and R⁸ can form a carbocycle, which can be saturated, unsaturated or aromatic and substituted or non substituted by halogen, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, or C₁-C₄-alkoxyalkyl; or R⁹ represents H, Cl, Br, I, cyano; phenyl; phenyl substituted by F, Cl, Br, I, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy; benzyl; benzyl substituted by F, Cl, Br, I, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy; C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-halo-genalkyl, C₁-C₄-halogenalkoxy or C₁-C₄-halogenalkylthio; C₁-C₄—COR¹⁴; —CR¹⁵═N—O—R¹⁶, COR¹⁴; or R¹⁰ represents H, Cl, Br, I, cyano; phenyl; phenyl substituted by F, Cl, Br, I, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy; benzyl; benzyl substituted by F, Cl, Br, I, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy; pyridyl; pyridyl substituted by F, Cl, Br, I, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy; C₁-C₆-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-halogenalkyl, C₁-C₄-halogenalkoxy or C₁-C₄-halogenalkylthio; C₁-C₄—S(O)_(m)R¹¹; C₁-C₄—SO₂NR¹²R¹³; C₁-C₄—COR¹⁴; —CR¹⁵═N—O—R¹⁶, S(O)_(m)R¹¹, SO₂NR¹²R¹³, COR¹⁴; or R¹¹ represents C₁-C₈-alkyl, C₃-C₆-cycloalkyl; or R¹² represents H, C₁-C₈-alkyl, C₃-C₆-cycloalkyl; or R¹³ represents H, C₁-C₈-alkyl, C₃-C₆-cycloalkyl; or R¹² and R¹³ can form a 5- or 6-membered heterocycle, which can further comprise one or more heteroatoms selected in the group consisting of O, N, and S; or R¹⁴ represents H, branched or linear C₁-C₈-alkyl, C₁-C₈-alkoxy; or R¹⁵ represents H, C₁-C₆-alkyl, C₃-C₆-cycloalkyl; or R¹⁶ represents H, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, benzyl; benzyl substituted by halogen, C₁-C₄-alkyl or C₁-C₄-halogenoalkyl; or R¹⁵ and R¹⁶ can form a 5- or 6-membered heterocycle optionally comprising a further heteroatom.
 3. A compound of formula (I) according to claim 1 wherein R¹ represents C₁-C₁₂-alkyl; or R³ represents a non substituted C₂-C₄-alkyl, C₃-C₄-alkenyl or cyclopropyl; or R² and R³ can form together a 6-membered heterocycle; or R⁴ represents a non substituted C₁-C₁₂-alkyl, a fluorine or a chlorine atom; or R⁵ represents a non substituted C₁-C₁₂-alkyl, a fluorine or a chlorine atom.
 4. A compound of formula (I) according to claim 1 wherein R¹ represents methyl; or R³ represents ethyl, n-propyl, i-propyl, propenyl or allyl; or R² and R³ can form together a piperidinyl or a pyrrolidinyl; or R⁴ represents methyl and ethyl; or R⁵ represents methyl or ethyl.
 5. A compound of formula (I) according to claim 1 wherein R² and R³ form together a 2-alkylated-pyrrolidinyl.
 6. A compound of formula (I) according to claim 5 wherein R² and R³ form together a 2-methyl-pyrrolidinyl.
 7. A process for the preparation of a compound of formula (I) according to claim 1 comprising at least one of the following steps:


8. A process for the preparation of a compound of formula (I) according to claim 1 comprising at least one of the following steps:


9. A method for controlling phytopathogenic fungi of crops, comprising applying an agronomically effective and substantially non-phytotoxic quantity of a compound according to claim 1 to soil where plants grow or is capable of growing, to leaves and/or to fruit of a plant or to seeds of a plant.
 10. A method for controlling damaging insects comprising applying a compound of formula (I) according to claim 1 to seed, a plant and/or to fruit of a plant or to soil wherein a plant is growing or wherein said plant is desired to grow. 